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When you upgrade Windows Server versions, especially when using AWS EC2, the server will often reboot and show the license agreement terms on the screen. this may be the problem You are required to accept these terms before you can proceed, but this can be difficult if you can't connect via RDP or use the AWS Systems Manager.
You can use EC2Rescue tool to diagnose the problem
https://docs.aws.amazon.com/AWSEC2/latest/WindowsGuide/Windows-Server-EC2Rescue.html
If all else fails, you can try detaching the root volume of the stuck instance and attaching it to another, functioning Windows instance. From there, you can access the file system and potentially bypass the license screen. Here are the steps:
- Stop both the stuck instance and the working instance.
- Detach the root volume of the stuck instance.
- Attach that volume to the working instance.
- On the working instance, look for the newly attached volume and note the drive letter it's been assigned.
- Try to navigate to drive letter:\Windows\System32\sysprep, find unattend.xml and remove it if it exists.
- Detach the volume from the working instance and re-attach it back to the original instance.
- Start the original instance.
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